# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Ivana Ivanovic-Burmazovic' _publ_contact_author_email IVANA.IVANOVIC@CHEMIE.UNI-ERLANGEN.DE _publ_section_title ; Chelate Electronic Properties control the Redox Behaviour and Superoxide Reactivity of Seven-Coordinate Manganese(II) Complexes ; loop_ _publ_author_name 'Ivana Ivanovic-Burmazovic' 'Katharina Durr' 'Frank W Heinemann' 'Gao-Feng Liu' 'Ralph Puchta' ; R.V.Eldik ; # Attachment 'CCDC_720837.cif' data_ii0407 _database_code_depnum_ccdc_archive 'CCDC 720837' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H21 Mn N7 O4, 2(C H4 O)' _chemical_formula_sum 'C21 H29 Mn N7 O6' _chemical_formula_weight 530.45 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall -C2yc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 25.251(2) _cell_length_b 7.6250(5) _cell_length_c 27.574(2) _cell_angle_alpha 90.00 _cell_angle_beta 113.044(5) _cell_angle_gamma 90.00 _cell_volume 4885.4(6) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 178 _cell_measurement_theta_min 6.00 _cell_measurement_theta_max 20.00 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.442 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2216 _exptl_absorpt_coefficient_mu 0.591 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.842 _exptl_absorpt_correction_T_max 0.960 _exptl_absorpt_process_details 'SADABS, Bruker-Nonius, 2002' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius KappaCCD' _diffrn_measurement_method ; \f- and \w-rotations with 1.20 \% and 96 sec per frame ; _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 55979 _diffrn_reflns_av_R_equivalents 0.0550 _diffrn_reflns_av_sigmaI/netI 0.0352 _diffrn_reflns_limit_h_min -32 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 3.21 _diffrn_reflns_theta_max 27.10 _reflns_number_total 5386 _reflns_number_gt 4235 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Bruker-Nonius, 2002)' _computing_cell_refinement 'EVALCCD (Bruker-Nonius, 2002)' _computing_data_reduction 'EVALCCD (Bruker-Nonius, 2002)' _computing_structure_solution 'SHELXTL 6.12 (Bruker AXS, 2002)' _computing_structure_refinement 'SHELXTL 6.12 (Bruker AXS, 2002)' _computing_molecular_graphics 'SHELXTL 6.12 (Bruker AXS, 2002)' _computing_publication_material 'SHELXTL 6.12 (Bruker AXS, 2002)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0259P)^2^+10.7249P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens 'difmap except free solvent molecules geom ' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5386 _refine_ls_number_parameters 383 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0602 _refine_ls_R_factor_gt 0.0396 _refine_ls_wR_factor_ref 0.0882 _refine_ls_wR_factor_gt 0.0827 _refine_ls_goodness_of_fit_ref 1.129 _refine_ls_restrained_S_all 1.129 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Mn1 Mn 0.621355(13) 0.91930(4) 0.437525(12) 0.01177(9) Uani 1 1 d . . . O1 O 0.80374(6) 1.07949(19) 0.52315(6) 0.0160(3) Uani 1 1 d . . . O2 O 0.57371(6) 1.0749(2) 0.27036(5) 0.0186(3) Uani 1 1 d . . . N1 N 0.68191(7) 1.0426(2) 0.40103(7) 0.0126(4) Uani 1 1 d . . . N2 N 0.71220(7) 0.9611(2) 0.49801(7) 0.0146(4) Uani 1 1 d . . . N3 N 0.72460(8) 0.9215(3) 0.55033(7) 0.0174(4) Uani 1 1 d . . . H3N H 0.7554(11) 0.959(3) 0.5737(10) 0.021 Uiso 1 1 d . . . N4 N 0.63805(8) 0.7705(2) 0.52172(7) 0.0169(4) Uani 1 1 d . . . N5 N 0.57435(7) 0.9834(2) 0.35093(7) 0.0133(4) Uani 1 1 d . . . N6 N 0.51534(7) 0.9549(2) 0.32756(7) 0.0149(4) Uani 1 1 d . . . H6N H 0.4968(10) 0.987(3) 0.2958(10) 0.018 Uiso 1 1 d . . . N7 N 0.52083(7) 0.9001(2) 0.41245(7) 0.0141(4) Uani 1 1 d . . . C1 C 0.66151(9) 1.0771(3) 0.34914(8) 0.0131(4) Uani 1 1 d . . . C2 C 0.69620(9) 1.1491(3) 0.32571(9) 0.0172(5) Uani 1 1 d . . . H2 H 0.6802(10) 1.168(3) 0.2881(10) 0.021 Uiso 1 1 d . . . C3 C 0.75275(10) 1.1904(3) 0.35779(9) 0.0203(5) Uani 1 1 d . . . H3 H 0.7762(10) 1.240(3) 0.3420(9) 0.024 Uiso 1 1 d . . . C4 C 0.77359(9) 1.1575(3) 0.41146(9) 0.0168(5) Uani 1 1 d . . . H4 H 0.8096(11) 1.189(3) 0.4329(9) 0.020 Uiso 1 1 d . . . C5 C 0.73671(9) 1.0814(3) 0.43174(8) 0.0132(4) Uani 1 1 d . . . C6 C 0.75354(9) 1.0387(3) 0.48872(8) 0.0130(4) Uani 1 1 d . . . C7 C 0.68602(9) 0.8253(3) 0.56224(8) 0.0157(5) Uani 1 1 d . . . C8 C 0.69732(11) 0.7856(3) 0.61541(9) 0.0215(5) Uani 1 1 d . . . H8 H 0.7303(11) 0.834(3) 0.6424(10) 0.026 Uiso 1 1 d . . . C9 C 0.65927(11) 0.6804(3) 0.62643(10) 0.0256(5) Uani 1 1 d . . . H9 H 0.6661(11) 0.652(4) 0.6629(11) 0.031 Uiso 1 1 d . . . C10 C 0.61124(11) 0.6139(3) 0.58478(10) 0.0244(5) Uani 1 1 d . . . H10 H 0.5845(11) 0.540(4) 0.5910(10) 0.029 Uiso 1 1 d . . . C11 C 0.60273(10) 0.6624(3) 0.53440(10) 0.0205(5) Uani 1 1 d . . . H11 H 0.5706(11) 0.617(3) 0.5063(10) 0.025 Uiso 1 1 d . . . C12 C 0.59822(9) 1.0423(3) 0.31973(8) 0.0134(4) Uani 1 1 d . . . C13 C 0.48815(9) 0.9275(3) 0.36085(8) 0.0135(4) Uani 1 1 d . . . C14 C 0.42733(9) 0.9299(3) 0.34077(9) 0.0179(5) Uani 1 1 d . . . H14 H 0.4074(10) 0.952(3) 0.3057(10) 0.022 Uiso 1 1 d . . . C15 C 0.40075(10) 0.9068(3) 0.37509(9) 0.0208(5) Uani 1 1 d . . . H15 H 0.3605(11) 0.911(3) 0.3627(10) 0.025 Uiso 1 1 d . . . C16 C 0.43380(10) 0.8814(3) 0.42889(9) 0.0202(5) Uani 1 1 d . . . H16 H 0.4167(10) 0.866(3) 0.4541(10) 0.024 Uiso 1 1 d . . . C17 C 0.49255(10) 0.8796(3) 0.44491(9) 0.0171(5) Uani 1 1 d . . . H17 H 0.5167(10) 0.865(3) 0.4808(10) 0.021 Uiso 1 1 d . . . O3 O 0.60967(6) 1.1932(2) 0.46518(6) 0.0153(3) Uani 1 1 d . . . H3O H 0.6379(11) 1.251(4) 0.4720(10) 0.023 Uiso 1 1 d . . . C18 C 0.55978(10) 1.2969(3) 0.43579(11) 0.0238(5) Uani 1 1 d . . . H18A H 0.5684(11) 1.424(4) 0.4397(10) 0.036 Uiso 1 1 d . . . H18B H 0.5429(11) 1.264(4) 0.3988(11) 0.036 Uiso 1 1 d . . . H18C H 0.5294(12) 1.278(4) 0.4492(10) 0.036 Uiso 1 1 d . . . O4 O 0.62938(7) 0.6525(2) 0.41140(6) 0.0177(3) Uani 1 1 d . . . H4O H 0.6537(11) 0.590(4) 0.4336(10) 0.027 Uiso 1 1 d . . . C19 C 0.62112(12) 0.5884(4) 0.36020(9) 0.0245(5) Uani 1 1 d . . . H19A H 0.5864(13) 0.634(4) 0.3349(11) 0.037 Uiso 1 1 d . . . H19B H 0.6198(12) 0.462(4) 0.3585(11) 0.037 Uiso 1 1 d . . . H19C H 0.6541(12) 0.630(4) 0.3480(11) 0.037 Uiso 1 1 d . . . O5 O 0.70415(8) 0.5265(2) 0.27430(8) 0.0378(5) Uani 1 1 d . . . H5 H 0.6722 0.4775 0.2671 0.057 Uiso 1 1 calc R . . C20 C 0.69546(12) 0.6956(4) 0.25254(10) 0.0364(7) Uani 1 1 d . . . H20A H 0.6767 0.7687 0.2704 0.055 Uiso 1 1 calc R . . H20B H 0.6710 0.6889 0.2149 0.055 Uiso 1 1 calc R . . H20C H 0.7326 0.7474 0.2572 0.055 Uiso 1 1 calc R . . O6 O 0.59442(8) 0.3903(3) 0.23829(9) 0.0529(6) Uani 1 1 d . . . H6 H 0.5872 0.2921 0.2481 0.079 Uiso 1 1 calc R . . C21 C 0.54454(14) 0.4626(5) 0.20298(14) 0.0594(10) Uani 1 1 d . . . H21A H 0.5443 0.5888 0.2097 0.089 Uiso 1 1 calc R . . H21B H 0.5115 0.4071 0.2069 0.089 Uiso 1 1 calc R . . H21C H 0.5422 0.4438 0.1671 0.089 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Mn1 0.01111(16) 0.01233(16) 0.01093(16) 0.00008(13) 0.00331(12) -0.00099(13) O1 0.0130(7) 0.0138(7) 0.0168(7) -0.0005(6) 0.0012(6) -0.0007(6) O2 0.0167(8) 0.0266(9) 0.0097(7) 0.0021(7) 0.0022(6) -0.0056(7) N1 0.0121(9) 0.0109(9) 0.0135(9) -0.0007(7) 0.0035(7) 0.0005(7) N2 0.0160(9) 0.0153(9) 0.0105(9) 0.0020(7) 0.0029(7) 0.0012(7) N3 0.0173(9) 0.0211(10) 0.0097(9) 0.0007(8) 0.0009(7) -0.0043(8) N4 0.0184(9) 0.0147(9) 0.0171(9) -0.0015(7) 0.0064(8) -0.0011(8) N5 0.0085(8) 0.0160(9) 0.0138(9) -0.0004(7) 0.0027(7) -0.0017(7) N6 0.0093(9) 0.0220(10) 0.0116(9) 0.0026(8) 0.0021(7) -0.0017(7) N7 0.0155(9) 0.0131(9) 0.0145(9) -0.0021(7) 0.0066(7) -0.0015(7) C1 0.0143(10) 0.0115(10) 0.0128(10) -0.0016(8) 0.0046(8) 0.0011(8) C2 0.0180(11) 0.0196(11) 0.0141(11) 0.0011(9) 0.0063(9) -0.0019(9) C3 0.0166(11) 0.0236(12) 0.0227(12) 0.0021(10) 0.0101(10) -0.0044(9) C4 0.0108(11) 0.0190(11) 0.0185(11) -0.0005(9) 0.0036(9) -0.0021(9) C5 0.0123(10) 0.0103(10) 0.0156(10) -0.0025(8) 0.0038(8) 0.0019(8) C6 0.0124(10) 0.0086(10) 0.0151(11) -0.0008(8) 0.0023(8) 0.0025(8) C7 0.0190(11) 0.0115(11) 0.0165(11) -0.0002(9) 0.0069(9) 0.0041(9) C8 0.0255(13) 0.0228(12) 0.0141(11) 0.0009(9) 0.0055(10) 0.0025(10) C9 0.0353(14) 0.0255(13) 0.0193(12) 0.0067(10) 0.0144(11) 0.0055(11) C10 0.0295(13) 0.0182(13) 0.0312(14) 0.0037(10) 0.0179(11) 0.0003(10) C11 0.0204(12) 0.0173(12) 0.0252(13) -0.0025(10) 0.0102(10) -0.0018(10) C12 0.0131(10) 0.0122(10) 0.0144(10) -0.0021(8) 0.0049(8) -0.0018(8) C13 0.0152(10) 0.0088(10) 0.0162(10) -0.0021(8) 0.0058(8) -0.0032(8) C14 0.0147(11) 0.0198(12) 0.0167(11) -0.0010(10) 0.0034(9) -0.0023(9) C15 0.0138(11) 0.0207(12) 0.0283(13) -0.0062(10) 0.0088(10) -0.0050(10) C16 0.0232(12) 0.0196(12) 0.0231(12) -0.0046(9) 0.0149(10) -0.0068(9) C17 0.0213(12) 0.0160(11) 0.0153(11) -0.0024(9) 0.0085(10) -0.0032(9) O3 0.0113(7) 0.0149(8) 0.0190(8) -0.0014(6) 0.0051(6) -0.0022(6) C18 0.0173(12) 0.0187(13) 0.0312(14) -0.0001(11) 0.0049(11) 0.0019(10) O4 0.0217(8) 0.0150(8) 0.0125(8) 0.0005(6) 0.0024(7) 0.0039(6) C19 0.0320(14) 0.0221(13) 0.0168(11) -0.0024(10) 0.0067(10) 0.0049(11) O5 0.0335(10) 0.0285(10) 0.0451(12) 0.0091(9) 0.0087(9) -0.0003(8) C20 0.0431(17) 0.0342(16) 0.0277(14) 0.0097(12) 0.0094(13) -0.0012(13) O6 0.0319(11) 0.0354(12) 0.0678(15) 0.0267(11) -0.0059(10) -0.0094(9) C21 0.0403(18) 0.054(2) 0.061(2) 0.0328(18) -0.0050(16) -0.0048(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Mn1 O4 2.1939(16) . ? Mn1 N5 2.2652(17) . ? Mn1 N2 2.2693(18) . ? Mn1 O3 2.2820(15) . ? Mn1 N1 2.3322(17) . ? Mn1 N7 2.3597(17) . ? Mn1 N4 2.4674(18) . ? O1 C6 1.290(2) . ? O2 C12 1.280(2) . ? N1 C5 1.342(3) . ? N1 C1 1.343(3) . ? N2 C6 1.310(3) . ? N2 N3 1.384(2) . ? N3 C7 1.359(3) . ? N3 H3N 0.84(3) . ? N4 C7 1.353(3) . ? N4 C11 1.357(3) . ? N5 C12 1.308(3) . ? N5 N6 1.390(2) . ? N6 C13 1.361(3) . ? N6 H6N 0.85(2) . ? N7 C13 1.353(3) . ? N7 C17 1.355(3) . ? C1 C2 1.389(3) . ? C1 C12 1.506(3) . ? C2 C3 1.390(3) . ? C2 H2 0.96(2) . ? C3 C4 1.386(3) . ? C3 H3 0.94(3) . ? C4 C5 1.387(3) . ? C4 H4 0.90(2) . ? C5 C6 1.494(3) . ? C7 C8 1.412(3) . ? C8 C9 1.374(3) . ? C8 H8 0.95(3) . ? C9 C10 1.399(4) . ? C9 H9 0.97(3) . ? C10 C11 1.371(3) . ? C10 H10 0.95(3) . ? C11 H11 0.94(3) . ? C13 C14 1.414(3) . ? C14 C15 1.369(3) . ? C14 H14 0.91(2) . ? C15 C16 1.402(3) . ? C15 H15 0.94(3) . ? C16 C17 1.372(3) . ? C16 H16 0.96(2) . ? C17 H17 0.94(2) . ? O3 C18 1.439(3) . ? O3 H3O 0.80(3) . ? C18 H18A 0.99(3) . ? C18 H18B 0.97(3) . ? C18 H18C 0.98(3) . ? O4 C19 1.430(3) . ? O4 H4O 0.83(3) . ? C19 H19A 0.95(3) . ? C19 H19B 0.96(3) . ? C19 H19C 1.06(3) . ? O5 C20 1.403(3) . ? O5 H5 0.8400 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? O6 C21 1.371(3) . ? O6 H6 0.8400 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O4 Mn1 N5 86.08(6) . . ? O4 Mn1 N2 100.07(6) . . ? N5 Mn1 N2 134.93(6) . . ? O4 Mn1 O3 177.62(6) . . ? N5 Mn1 O3 94.12(6) . . ? N2 Mn1 O3 81.47(6) . . ? O4 Mn1 N1 94.11(6) . . ? N5 Mn1 N1 67.64(6) . . ? N2 Mn1 N1 67.41(6) . . ? O3 Mn1 N1 88.15(6) . . ? O4 Mn1 N7 94.20(6) . . ? N5 Mn1 N7 69.20(6) . . ? N2 Mn1 N7 152.37(6) . . ? O3 Mn1 N7 83.67(6) . . ? N1 Mn1 N7 135.26(6) . . ? O4 Mn1 N4 83.04(6) . . ? N5 Mn1 N4 156.51(6) . . ? N2 Mn1 N4 67.77(6) . . ? O3 Mn1 N4 95.93(6) . . ? N1 Mn1 N4 133.78(6) . . ? N7 Mn1 N4 90.87(6) . . ? C5 N1 C1 119.96(18) . . ? C5 N1 Mn1 120.31(13) . . ? C1 N1 Mn1 119.72(13) . . ? C6 N2 N3 115.46(18) . . ? C6 N2 Mn1 124.99(14) . . ? N3 N2 Mn1 119.12(13) . . ? C7 N3 N2 118.58(18) . . ? C7 N3 H3N 122.3(17) . . ? N2 N3 H3N 119.1(17) . . ? C7 N4 C11 116.16(19) . . ? C7 N4 Mn1 113.78(14) . . ? C11 N4 Mn1 129.36(15) . . ? C12 N5 N6 115.81(17) . . ? C12 N5 Mn1 125.53(14) . . ? N6 N5 Mn1 118.63(12) . . ? C13 N6 N5 116.35(17) . . ? C13 N6 H6N 121.2(16) . . ? N5 N6 H6N 119.3(16) . . ? C13 N7 C17 116.76(18) . . ? C13 N7 Mn1 116.24(13) . . ? C17 N7 Mn1 126.74(14) . . ? N1 C1 C2 121.61(19) . . ? N1 C1 C12 115.00(18) . . ? C2 C1 C12 123.29(18) . . ? C1 C2 C3 118.1(2) . . ? C1 C2 H2 118.8(14) . . ? C3 C2 H2 123.0(14) . . ? C4 C3 C2 120.3(2) . . ? C4 C3 H3 121.5(15) . . ? C2 C3 H3 118.1(15) . . ? C3 C4 C5 118.2(2) . . ? C3 C4 H4 121.2(15) . . ? C5 C4 H4 120.6(15) . . ? N1 C5 C4 121.79(19) . . ? N1 C5 C6 114.45(18) . . ? C4 C5 C6 123.75(19) . . ? O1 C6 N2 126.45(19) . . ? O1 C6 C5 120.96(18) . . ? N2 C6 C5 112.58(18) . . ? N4 C7 N3 117.51(19) . . ? N4 C7 C8 122.9(2) . . ? N3 C7 C8 119.6(2) . . ? C9 C8 C7 118.7(2) . . ? C9 C8 H8 121.8(15) . . ? C7 C8 H8 119.5(16) . . ? C8 C9 C10 119.1(2) . . ? C8 C9 H9 120.1(16) . . ? C10 C9 H9 120.8(16) . . ? C11 C10 C9 118.4(2) . . ? C11 C10 H10 120.3(16) . . ? C9 C10 H10 121.3(16) . . ? N4 C11 C10 124.5(2) . . ? N4 C11 H11 116.8(15) . . ? C10 C11 H11 118.6(16) . . ? O2 C12 N5 127.63(19) . . ? O2 C12 C1 120.53(18) . . ? N5 C12 C1 111.81(17) . . ? N7 C13 N6 118.17(18) . . ? N7 C13 C14 122.40(19) . . ? N6 C13 C14 119.43(19) . . ? C15 C14 C13 118.6(2) . . ? C15 C14 H14 122.6(15) . . ? C13 C14 H14 118.7(15) . . ? C14 C15 C16 120.0(2) . . ? C14 C15 H15 119.9(15) . . ? C16 C15 H15 120.1(15) . . ? C17 C16 C15 117.6(2) . . ? C17 C16 H16 120.1(15) . . ? C15 C16 H16 122.3(15) . . ? N7 C17 C16 124.7(2) . . ? N7 C17 H17 114.5(14) . . ? C16 C17 H17 120.8(14) . . ? C18 O3 Mn1 120.93(14) . . ? C18 O3 H3O 109.5(19) . . ? Mn1 O3 H3O 111.4(19) . . ? O3 C18 H18A 111.7(16) . . ? O3 C18 H18B 112.2(16) . . ? H18A C18 H18B 111(2) . . ? O3 C18 H18C 110.3(16) . . ? H18A C18 H18C 106(2) . . ? H18B C18 H18C 106(2) . . ? C19 O4 Mn1 130.13(14) . . ? C19 O4 H4O 108.2(18) . . ? Mn1 O4 H4O 115.4(18) . . ? O4 C19 H19A 109.7(17) . . ? O4 C19 H19B 112.2(16) . . ? H19A C19 H19B 109(2) . . ? O4 C19 H19C 112.4(15) . . ? H19A C19 H19C 106(2) . . ? H19B C19 H19C 107(2) . . ? C20 O5 H5 109.5 . . ? O5 C20 H20A 109.5 . . ? O5 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? O5 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C21 O6 H6 109.5 . . ? O6 C21 H21A 109.5 . . ? O6 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? O6 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O3 H3O O1 0.80(3) 1.92(3) 2.709(2) 168(3) 7_676 O4 H4O O1 0.83(3) 1.80(3) 2.617(2) 169(3) 7_666 N6 H6N O2 0.85(2) 2.10(3) 2.904(2) 157(2) 2_655 O5 H5 O6 0.84 1.93 2.755(3) 169.1 . O6 H6 O2 0.84 1.84 2.683(2) 178.3 1_545 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.10 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.344 _refine_diff_density_min -0.311 _refine_diff_density_rms 0.064 #===END OF ALL DATA # Attachment 'CCDC_720838.cif' data_ii0301 _database_code_depnum_ccdc_archive 'CCDC 720838' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H23 Mn N7 O2, 2(Cl O4)' _chemical_formula_sum 'C19 H23 Cl2 Mn N7 O10' _chemical_formula_weight 635.28 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall -C2yc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 10.9947(6) _cell_length_b 31.380(4) _cell_length_c 7.9492(6) _cell_angle_alpha 90.00 _cell_angle_beta 108.613(5) _cell_angle_gamma 90.00 _cell_volume 2599.1(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 247 _cell_measurement_theta_min 6.00 _cell_measurement_theta_max 20.00 _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.623 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1300 _exptl_absorpt_coefficient_mu 0.780 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 1 0 0 0.065 -1 0 0 0.110 0 1 0 0.135 0 -1 0 0.110 0 0 1 0.155 0 0 -1 0.120 -2 -3 0 0.085 3 -4 0 0.022 0 -3 -1 0.082 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.826 _exptl_absorpt_correction_T_max 0.902 _exptl_absorpt_process_details ; Gaussian integration (Coppens, 1970) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius KappaCCD' _diffrn_measurement_method ; \f- and \w-rotations with 2.0 \% and 40 sec per frame ; _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 31490 _diffrn_reflns_av_R_equivalents 0.0653 _diffrn_reflns_av_sigmaI/netI 0.0400 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -41 _diffrn_reflns_limit_k_max 41 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.40 _diffrn_reflns_theta_max 27.87 _reflns_number_total 3105 _reflns_number_gt 2482 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Bruker-Nonius, 2002)' _computing_cell_refinement 'EVALCCD (Bruker-Nonius, 2002)' _computing_data_reduction 'EVALCCD (Bruker-Nonius, 2002)' _computing_structure_solution 'SHELXTL 6.12 (Bruker AXS, 2002)' _computing_structure_refinement 'SHELXTL 6.12 (Bruker AXS, 2002)' _computing_molecular_graphics 'SHELXTL 6.12 (Bruker AXS, 2002)' _computing_publication_material 'SHELXTL 6.12 (Bruker AXS, 2002)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0346P)^2^+3.0702P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refxyz _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3105 _refine_ls_number_parameters 212 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0538 _refine_ls_R_factor_gt 0.0331 _refine_ls_wR_factor_ref 0.0754 _refine_ls_wR_factor_gt 0.0701 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Mn1 Mn 1.0000 0.138676(12) 0.2500 0.00904(11) Uani 1 2 d S . . N1 N 1.0000 0.06496(7) 0.2500 0.0124(5) Uani 1 2 d S . . N2 N 0.79425(14) 0.11025(5) 0.13769(19) 0.0108(3) Uani 1 1 d . . . N3 N 0.69640(15) 0.13858(5) 0.0832(2) 0.0128(3) Uani 1 1 d . . . H3N H 0.623(2) 0.1312(7) 0.040(3) 0.015 Uiso 1 1 d . . . N4 N 0.84339(14) 0.19033(5) 0.2279(2) 0.0116(3) Uani 1 1 d . . . O1 O 1.01808(14) 0.14486(5) 0.53460(18) 0.0163(3) Uani 1 1 d . . . H1A H 1.067(2) 0.1299(7) 0.616(3) 0.020 Uiso 1 1 d . . . H1B H 0.953(2) 0.1430(7) 0.553(3) 0.020 Uiso 1 1 d . . . C3 C 1.0000 -0.02280(10) 0.2500 0.0439(11) Uani 1 2 d S . . H3 H 1.0000 -0.0542(13) 0.2500 0.053 Uiso 1 2 d S . . C4 C 0.8863(2) -0.00085(7) 0.1766(4) 0.0303(6) Uani 1 1 d . . . H4 H 0.812(3) -0.0146(8) 0.124(3) 0.036 Uiso 1 1 d . . . C5 C 0.88920(17) 0.04338(6) 0.1789(3) 0.0152(4) Uani 1 1 d . . . C6 C 0.77287(17) 0.06997(6) 0.1086(2) 0.0127(4) Uani 1 1 d . . . C7 C 0.72095(17) 0.18003(6) 0.1434(2) 0.0115(4) Uani 1 1 d . . . C8 C 0.6186(2) 0.20876(6) 0.1171(3) 0.0166(4) Uani 1 1 d . . . H8 H 0.536(2) 0.1997(7) 0.056(3) 0.020 Uiso 1 1 d . . . C9 C 0.6463(2) 0.24930(6) 0.1841(3) 0.0195(4) Uani 1 1 d . . . H9 H 0.584(2) 0.2691(7) 0.169(3) 0.023 Uiso 1 1 d . . . C10 C 0.7723(2) 0.26042(7) 0.2778(3) 0.0191(4) Uani 1 1 d . . . H10 H 0.794(2) 0.2871(7) 0.325(3) 0.023 Uiso 1 1 d . . . C11 C 0.86588(19) 0.23018(6) 0.2964(3) 0.0156(4) Uani 1 1 d . . . H11 H 0.953(2) 0.2364(7) 0.359(3) 0.019 Uiso 1 1 d . . . C13 C 0.64338(19) 0.05141(7) 0.0160(3) 0.0196(4) Uani 1 1 d . . . H13A H 0.602(2) 0.0657(8) -0.092(3) 0.029 Uiso 1 1 d . . . H13B H 0.649(2) 0.0221(8) -0.005(3) 0.029 Uiso 1 1 d . . . H13C H 0.586(2) 0.0557(8) 0.082(3) 0.029 Uiso 1 1 d . . . Cl1 Cl 0.69552(4) 0.111538(14) -0.42303(6) 0.01169(11) Uani 1 1 d . . . O11 O 0.65709(14) 0.07866(5) -0.55430(18) 0.0238(3) Uani 1 1 d . . . O12 O 0.58622(13) 0.12833(5) -0.38235(19) 0.0219(3) Uani 1 1 d . . . O13 O 0.78657(13) 0.09422(4) -0.26279(18) 0.0211(3) Uani 1 1 d . . . O14 O 0.75783(14) 0.14595(4) -0.4853(2) 0.0235(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Mn1 0.0074(2) 0.00860(19) 0.0103(2) 0.000 0.00159(15) 0.000 N1 0.0098(11) 0.0109(11) 0.0159(11) 0.000 0.0032(9) 0.000 N2 0.0085(7) 0.0118(8) 0.0116(8) 0.0015(6) 0.0025(6) 0.0024(6) N3 0.0058(7) 0.0124(8) 0.0170(8) -0.0005(6) -0.0010(6) 0.0003(6) N4 0.0110(8) 0.0118(8) 0.0121(8) 0.0003(6) 0.0038(6) 0.0001(6) O1 0.0121(7) 0.0233(8) 0.0130(7) 0.0028(6) 0.0034(6) 0.0021(6) C3 0.0192(17) 0.0093(15) 0.094(3) 0.000 0.0044(19) 0.000 C4 0.0102(10) 0.0125(10) 0.0609(17) -0.0021(10) 0.0013(10) -0.0029(8) C5 0.0096(9) 0.0119(9) 0.0230(10) -0.0005(8) 0.0037(8) -0.0014(7) C6 0.0100(9) 0.0126(9) 0.0154(9) -0.0011(7) 0.0041(8) -0.0017(7) C7 0.0117(9) 0.0123(9) 0.0108(9) 0.0025(7) 0.0040(7) 0.0008(7) C8 0.0121(9) 0.0165(10) 0.0196(10) 0.0019(8) 0.0028(8) 0.0042(8) C9 0.0196(11) 0.0163(10) 0.0229(11) 0.0019(8) 0.0072(9) 0.0093(8) C10 0.0227(11) 0.0130(10) 0.0214(11) -0.0037(8) 0.0070(9) 0.0018(8) C11 0.0155(10) 0.0141(9) 0.0162(10) -0.0024(7) 0.0037(8) -0.0015(8) C13 0.0111(10) 0.0132(10) 0.0306(12) -0.0031(8) 0.0013(9) -0.0025(8) Cl1 0.0089(2) 0.0130(2) 0.0125(2) -0.00028(16) 0.00249(17) 0.00036(16) O11 0.0224(8) 0.0255(8) 0.0203(8) -0.0108(6) 0.0022(6) -0.0029(6) O12 0.0114(7) 0.0267(8) 0.0282(8) -0.0054(6) 0.0072(6) 0.0012(6) O13 0.0207(8) 0.0186(7) 0.0184(7) 0.0012(6) -0.0016(6) 0.0040(6) O14 0.0248(8) 0.0195(8) 0.0312(8) 0.0050(6) 0.0158(7) -0.0019(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Mn1 O1 2.2155(14) . ? Mn1 O1 2.2155(14) 2_755 ? Mn1 N1 2.313(2) . ? Mn1 N2 2.3282(15) . ? Mn1 N2 2.3282(15) 2_755 ? Mn1 N4 2.3302(15) 2_755 ? Mn1 N4 2.3302(15) . ? N1 C5 1.350(2) . ? N1 C5 1.350(2) 2_755 ? N2 C6 1.293(2) . ? N2 N3 1.356(2) . ? N3 C7 1.382(2) . ? N3 H3N 0.80(2) . ? N4 C7 1.338(2) . ? N4 C11 1.355(2) . ? O1 H1A 0.84(2) . ? O1 H1B 0.77(2) . ? C3 C4 1.383(3) 2_755 ? C3 C4 1.383(3) . ? C3 H3 0.98(4) . ? C4 C5 1.388(3) . ? C4 H4 0.90(3) . ? C5 C6 1.479(3) . ? C6 C13 1.496(3) . ? C7 C8 1.405(3) . ? C8 C9 1.375(3) . ? C8 H8 0.92(2) . ? C9 C10 1.392(3) . ? C9 H9 0.90(2) . ? C10 C11 1.373(3) . ? C10 H10 0.92(2) . ? C11 H11 0.95(2) . ? C13 H13A 0.94(2) . ? C13 H13B 0.94(2) . ? C13 H13C 0.96(2) . ? Cl1 O11 1.4319(14) . ? Cl1 O12 1.4403(14) . ? Cl1 O14 1.4479(14) . ? Cl1 O13 1.4512(14) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Mn1 O1 169.95(8) . 2_755 ? O1 Mn1 N1 95.02(4) . . ? O1 Mn1 N1 95.02(4) 2_755 . ? O1 Mn1 N2 100.64(5) . . ? O1 Mn1 N2 83.25(5) 2_755 . ? N1 Mn1 N2 67.47(4) . . ? O1 Mn1 N2 83.25(5) . 2_755 ? O1 Mn1 N2 100.64(5) 2_755 2_755 ? N1 Mn1 N2 67.47(4) . 2_755 ? N2 Mn1 N2 134.95(7) . 2_755 ? O1 Mn1 N4 92.22(5) . 2_755 ? O1 Mn1 N4 80.76(5) 2_755 2_755 ? N1 Mn1 N4 134.07(4) . 2_755 ? N2 Mn1 N4 154.10(5) . 2_755 ? N2 Mn1 N4 68.49(5) 2_755 2_755 ? O1 Mn1 N4 80.76(5) . . ? O1 Mn1 N4 92.22(5) 2_755 . ? N1 Mn1 N4 134.07(4) . . ? N2 Mn1 N4 68.49(5) . . ? N2 Mn1 N4 154.10(5) 2_755 . ? N4 Mn1 N4 91.85(7) 2_755 . ? C5 N1 C5 119.8(2) . 2_755 ? C5 N1 Mn1 120.11(11) . . ? C5 N1 Mn1 120.11(11) 2_755 . ? C6 N2 N3 120.23(15) . . ? C6 N2 Mn1 122.82(12) . . ? N3 N2 Mn1 116.50(11) . . ? N2 N3 C7 117.32(15) . . ? N2 N3 H3N 122.2(16) . . ? C7 N3 H3N 118.6(15) . . ? C7 N4 C11 116.75(16) . . ? C7 N4 Mn1 118.07(12) . . ? C11 N4 Mn1 125.17(13) . . ? Mn1 O1 H1A 124.2(15) . . ? Mn1 O1 H1B 113.6(17) . . ? H1A O1 H1B 102(2) . . ? C4 C3 C4 120.2(3) 2_755 . ? C4 C3 H3 119.88(15) 2_755 . ? C4 C3 H3 119.88(15) . . ? C3 C4 C5 118.6(2) . . ? C3 C4 H4 121.5(16) . . ? C5 C4 H4 119.9(16) . . ? N1 C5 C4 121.39(18) . . ? N1 C5 C6 115.53(16) . . ? C4 C5 C6 123.07(17) . . ? N2 C6 C5 113.45(16) . . ? N2 C6 C13 123.97(17) . . ? C5 C6 C13 122.57(16) . . ? N4 C7 N3 117.07(16) . . ? N4 C7 C8 123.33(17) . . ? N3 C7 C8 119.59(17) . . ? C9 C8 C7 117.91(19) . . ? C9 C8 H8 123.2(14) . . ? C7 C8 H8 118.9(14) . . ? C8 C9 C10 119.94(19) . . ? C8 C9 H9 121.3(14) . . ? C10 C9 H9 118.7(14) . . ? C11 C10 C9 117.91(19) . . ? C11 C10 H10 120.0(14) . . ? C9 C10 H10 122.1(14) . . ? N4 C11 C10 124.09(18) . . ? N4 C11 H11 115.1(13) . . ? C10 C11 H11 120.8(13) . . ? C6 C13 H13A 111.5(14) . . ? C6 C13 H13B 111.4(15) . . ? H13A C13 H13B 110(2) . . ? C6 C13 H13C 111.7(14) . . ? H13A C13 H13C 103(2) . . ? H13B C13 H13C 109(2) . . ? O11 Cl1 O12 110.72(9) . . ? O11 Cl1 O14 110.49(9) . . ? O12 Cl1 O14 108.88(9) . . ? O11 Cl1 O13 109.29(9) . . ? O12 Cl1 O13 109.34(9) . . ? O14 Cl1 O13 108.07(9) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1A O13 0.84(2) 2.00(2) 2.818(2) 164(2) 2_755 O1 H1B O14 0.77(2) 2.08(2) 2.815(2) 160(2) 1_556 N3 H3N O12 0.80(2) 2.24(2) 3.023(2) 164(2) 2_654 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.87 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.423 _refine_diff_density_min -0.609 _refine_diff_density_rms 0.145 #===END OF ALL DATA # Attachment 'CCDC_720839.cif' data_lg0401 _database_code_depnum_ccdc_archive 'CCDC 720839' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H15 N7 O2, H2 O' _chemical_formula_sum 'C17 H17 N7 O3' _chemical_formula_weight 367.38 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/n _symmetry_space_group_name_Hall -P2yn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.9352(9) _cell_length_b 8.3106(3) _cell_length_c 17.982(2) _cell_angle_alpha 90.00 _cell_angle_beta 102.780(7) _cell_angle_gamma 90.00 _cell_volume 1739.4(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 220 _cell_measurement_theta_min 6.00 _cell_measurement_theta_max 20.00 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.403 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 0.101 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 1 0 0 0.050 -1 0 0 0.100 0 1 0 0.100 0 -1 0 0.100 0 0 1 0.080 0 0 -1 0.140 0 6 7 0.083 0 1 -2 0.130 0 -1 -2 0.097 0 -1 2 0.084 1 0 -1 0.040 -1 0 1 0.080 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.982 _exptl_absorpt_correction_T_max 0.990 _exptl_absorpt_process_details ; Gaussian integration (Coppens, 1970) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius KappaCCD' _diffrn_measurement_method ; \w-rotations with 2.00 \% and 80 sec per frame ; _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26980 _diffrn_reflns_av_R_equivalents 0.0832 _diffrn_reflns_av_sigmaI/netI 0.0469 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.50 _diffrn_reflns_theta_max 27.10 _reflns_number_total 3843 _reflns_number_gt 2853 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Bruker-Nonius, 2002)' _computing_cell_refinement 'EVALCCD (Duisenberg, 2003)' _computing_data_reduction 'EVALCCD (Duisenberg, 2003)' _computing_structure_solution 'SHELXTL 6.12 (Bruker AXS, 2002)' _computing_structure_refinement 'SHELXTL 6.12 (Bruker AXS, 2002)' _computing_molecular_graphics 'SHELXTL 6.12 (Bruker AXS, 2002)' _computing_publication_material 'SHELXTL 6.12 (Bruker AXS, 2002)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0470P)^2^+0.7000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3843 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0756 _refine_ls_R_factor_gt 0.0463 _refine_ls_wR_factor_ref 0.1051 _refine_ls_wR_factor_gt 0.0949 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.68444(11) 0.75016(15) 0.53651(6) 0.0208(3) Uani 1 1 d . . . O2 O 0.64817(9) 1.17521(14) 0.19519(6) 0.0148(3) Uani 1 1 d . . . N1 N 0.69288(11) 0.92367(16) 0.35822(7) 0.0130(3) Uani 1 1 d . . . N2 N 0.80803(12) 0.71084(17) 0.45785(7) 0.0146(3) Uani 1 1 d . . . H2N H 0.8162 0.7142 0.4087 0.017 Uiso 1 1 d . . . N3 N 0.88020(11) 0.60897(17) 0.50778(7) 0.0161(3) Uani 1 1 d . . . H3N H 0.9343 0.6633 0.5428 0.019 Uiso 1 1 d . . . N4 N 0.74975(11) 0.39757(17) 0.47673(7) 0.0149(3) Uani 1 1 d . . . N5 N 0.78665(11) 0.98841(16) 0.24079(7) 0.0135(3) Uani 1 1 d . . . H5N H 0.8059 0.9047 0.2716 0.016 Uiso 1 1 d . . . N6 N 0.84265(11) 1.00616(18) 0.18135(7) 0.0163(3) Uani 1 1 d . . . H6N H 0.8102 0.9662 0.1359 0.020 Uiso 1 1 d . . . N7 N 1.00486(11) 1.11084(18) 0.26358(7) 0.0173(3) Uani 1 1 d . . . C1 C 0.63275(13) 1.02022(19) 0.30439(8) 0.0126(3) Uani 1 1 d . . . C2 C 0.52195(14) 1.0727(2) 0.30366(9) 0.0170(4) Uani 1 1 d . . . H2 H 0.4811 1.1426 0.2627 0.020 Uiso 1 1 d . . . C3 C 0.46906(14) 1.0167(2) 0.36026(9) 0.0199(4) Uani 1 1 d . . . H3 H 0.3926 1.0517 0.3612 0.024 Uiso 1 1 d . . . C4 C 0.52978(14) 0.9151(2) 0.41564(9) 0.0171(4) Uani 1 1 d . . . H4 H 0.4966 0.8718 0.4564 0.021 Uiso 1 1 d . . . C5 C 0.64183(13) 0.87355(19) 0.41333(8) 0.0137(3) Uani 1 1 d . . . C6 C 0.71231(14) 0.77078(19) 0.47553(9) 0.0142(3) Uani 1 1 d . . . C7 C 0.84283(13) 0.4595(2) 0.52328(9) 0.0136(3) Uani 1 1 d . . . C8 C 0.90764(14) 0.3750(2) 0.58615(9) 0.0182(4) Uani 1 1 d . . . H8 H 0.9758 0.4248 0.6164 0.022 Uiso 1 1 d . . . C9 C 0.87378(16) 0.2229(2) 0.60025(10) 0.0240(4) Uani 1 1 d . . . H9 H 0.9169 0.1611 0.6418 0.029 Uiso 1 1 d . . . C10 C 0.77487(16) 0.1567(2) 0.55301(10) 0.0237(4) Uani 1 1 d . . . H10 H 0.7481 0.0466 0.5615 0.028 Uiso 1 1 d . . . C11 C 0.71815(15) 0.2484(2) 0.49309(9) 0.0188(4) Uani 1 1 d . . . H11 H 0.6488 0.2035 0.4579 0.023 Uiso 1 1 d . . . C12 C 0.69075(13) 1.07007(19) 0.24160(8) 0.0127(3) Uani 1 1 d . . . C13 C 0.95773(14) 1.04190(19) 0.19674(9) 0.0137(3) Uani 1 1 d . . . C14 C 1.02079(15) 1.0081(2) 0.14106(9) 0.0182(4) Uani 1 1 d . . . H14 H 0.9807 0.9598 0.0944 0.022 Uiso 1 1 d . . . C15 C 1.13471(15) 1.0494(2) 0.15556(10) 0.0234(4) Uani 1 1 d . . . H15 H 1.1801 1.0284 0.1183 0.028 Uiso 1 1 d . . . C16 C 1.18459(15) 1.1251(3) 0.22425(10) 0.0268(4) Uani 1 1 d . . . H16 H 1.2685 1.1640 0.2339 0.032 Uiso 1 1 d . . . C17 C 1.11707(15) 1.1517(2) 0.27594(9) 0.0226(4) Uani 1 1 d . . . H17 H 1.1492 1.2065 0.3259 0.027 Uiso 1 1 d . . . O3 O 1.07027(12) 0.75277(19) 0.61533(7) 0.0263(4) Uani 0.87 1 d P A 1 H3A H 1.0606 0.7936 0.6523 0.039 Uiso 0.87 1 d P B 1 H3B H 1.1158 0.8073 0.6020 0.039 Uiso 0.87 1 d P C 1 O3A O 1.0476(8) 0.9000(13) 0.5680(5) 0.026(2) Uani 0.13 1 d P D 2 H3C H 1.0016 0.9162 0.5130 0.039 Uiso 0.13 1 d P E 2 H3D H 1.0681 0.9971 0.6105 0.039 Uiso 0.13 1 d P F 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0300(7) 0.0202(7) 0.0151(6) 0.0022(5) 0.0116(5) 0.0022(5) O2 0.0155(6) 0.0159(6) 0.0130(5) 0.0024(5) 0.0029(4) -0.0008(5) N1 0.0154(7) 0.0129(7) 0.0115(6) -0.0010(5) 0.0047(5) -0.0004(5) N2 0.0172(7) 0.0159(7) 0.0106(6) 0.0029(5) 0.0030(5) 0.0022(6) N3 0.0138(7) 0.0189(8) 0.0139(6) 0.0033(6) -0.0004(5) -0.0017(6) N4 0.0149(7) 0.0172(7) 0.0133(6) -0.0005(6) 0.0045(5) 0.0011(6) N5 0.0134(7) 0.0168(7) 0.0114(6) 0.0032(6) 0.0052(5) 0.0009(6) N6 0.0142(7) 0.0271(8) 0.0086(6) -0.0014(6) 0.0043(5) -0.0019(6) N7 0.0152(7) 0.0213(8) 0.0151(7) 0.0006(6) 0.0027(6) -0.0009(6) C1 0.0140(8) 0.0117(8) 0.0122(7) -0.0024(6) 0.0028(6) -0.0026(6) C2 0.0144(8) 0.0195(9) 0.0165(8) 0.0018(7) 0.0024(7) 0.0009(7) C3 0.0134(8) 0.0268(10) 0.0210(8) -0.0007(7) 0.0069(7) 0.0004(7) C4 0.0196(9) 0.0181(9) 0.0161(8) -0.0015(7) 0.0088(7) -0.0024(7) C5 0.0170(8) 0.0124(8) 0.0127(7) -0.0025(6) 0.0051(6) -0.0028(7) C6 0.0189(8) 0.0113(8) 0.0131(7) -0.0021(6) 0.0054(7) -0.0029(7) C7 0.0121(8) 0.0173(9) 0.0131(7) -0.0007(6) 0.0062(6) 0.0025(6) C8 0.0164(8) 0.0220(9) 0.0150(8) 0.0007(7) 0.0010(6) 0.0016(7) C9 0.0276(10) 0.0227(10) 0.0197(8) 0.0063(7) 0.0010(8) 0.0050(8) C10 0.0307(10) 0.0163(9) 0.0237(9) 0.0016(7) 0.0053(8) -0.0025(8) C11 0.0207(9) 0.0190(9) 0.0170(8) -0.0039(7) 0.0049(7) -0.0030(7) C12 0.0124(8) 0.0133(8) 0.0118(7) -0.0018(6) 0.0013(6) -0.0034(6) C13 0.0143(8) 0.0129(8) 0.0139(7) 0.0043(6) 0.0033(6) 0.0029(6) C14 0.0198(9) 0.0194(9) 0.0168(8) 0.0015(7) 0.0072(7) 0.0017(7) C15 0.0187(9) 0.0302(11) 0.0243(9) 0.0062(8) 0.0111(7) 0.0049(8) C16 0.0133(8) 0.0396(12) 0.0271(9) 0.0060(9) 0.0037(7) -0.0015(8) C17 0.0165(9) 0.0308(11) 0.0194(8) 0.0006(8) 0.0015(7) -0.0040(8) O3 0.0215(8) 0.0395(9) 0.0208(7) -0.0211(7) 0.0111(6) -0.0129(7) O3A 0.022(5) 0.041(6) 0.018(4) -0.021(5) 0.010(4) -0.014(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C6 1.2262(19) . ? O2 C12 1.2371(19) . ? N1 C1 1.337(2) . ? N1 C5 1.339(2) . ? N2 C6 1.347(2) . ? N2 N3 1.3866(18) . ? N2 H2N 0.9115 . ? N3 C7 1.369(2) . ? N3 H3N 0.9155 . ? N4 C7 1.337(2) . ? N4 C11 1.347(2) . ? N5 C12 1.333(2) . ? N5 N6 1.3881(17) . ? N5 H5N 0.8874 . ? N6 C13 1.372(2) . ? N6 H6N 0.8876 . ? N7 C13 1.338(2) . ? N7 C17 1.351(2) . ? C1 C2 1.390(2) . ? C1 C12 1.507(2) . ? C2 C3 1.391(2) . ? C2 H2 0.9791 . ? C3 C4 1.383(2) . ? C3 H3 0.9616 . ? C4 C5 1.391(2) . ? C4 H4 0.9752 . ? C5 C6 1.507(2) . ? C7 C8 1.408(2) . ? C8 C9 1.367(3) . ? C8 H8 0.9664 . ? C9 C10 1.405(3) . ? C9 H9 0.9585 . ? C10 C11 1.370(2) . ? C10 H10 0.9920 . ? C11 H11 0.9960 . ? C13 C14 1.407(2) . ? C14 C15 1.370(2) . ? C14 H14 0.9576 . ? C15 C16 1.397(3) . ? C15 H15 0.9660 . ? C16 C17 1.376(3) . ? C16 H16 1.0297 . ? C17 H17 1.0049 . ? O3 H3A 0.7773 . ? O3 H3B 0.7847 . ? O3A H3B 1.1868 . ? O3A H3C 1.0291 . ? O3A H3D 1.1006 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C5 117.58(14) . . ? C6 N2 N3 120.72(13) . . ? C6 N2 H2N 119.7 . . ? N3 N2 H2N 117.6 . . ? C7 N3 N2 120.14(13) . . ? C7 N3 H3N 121.3 . . ? N2 N3 H3N 112.8 . . ? C7 N4 C11 116.84(14) . . ? C12 N5 N6 120.99(13) . . ? C12 N5 H5N 119.7 . . ? N6 N5 H5N 117.5 . . ? C13 N6 N5 119.92(12) . . ? C13 N6 H6N 118.7 . . ? N5 N6 H6N 118.9 . . ? C13 N7 C17 117.37(14) . . ? N1 C1 C2 123.52(14) . . ? N1 C1 C12 116.44(14) . . ? C2 C1 C12 120.03(14) . . ? C1 C2 C3 118.24(15) . . ? C1 C2 H2 120.6 . . ? C3 C2 H2 121.1 . . ? C4 C3 C2 118.74(15) . . ? C4 C3 H3 121.4 . . ? C2 C3 H3 119.8 . . ? C3 C4 C5 118.97(15) . . ? C3 C4 H4 122.1 . . ? C5 C4 H4 119.0 . . ? N1 C5 C4 122.88(15) . . ? N1 C5 C6 117.05(14) . . ? C4 C5 C6 120.06(14) . . ? O1 C6 N2 124.83(15) . . ? O1 C6 C5 121.70(15) . . ? N2 C6 C5 113.43(13) . . ? N4 C7 N3 119.00(14) . . ? N4 C7 C8 122.91(15) . . ? N3 C7 C8 118.03(14) . . ? C9 C8 C7 118.51(15) . . ? C9 C8 H8 122.5 . . ? C7 C8 H8 118.9 . . ? C8 C9 C10 119.54(16) . . ? C8 C9 H9 120.7 . . ? C10 C9 H9 119.8 . . ? C11 C10 C9 117.42(16) . . ? C11 C10 H10 121.0 . . ? C9 C10 H10 121.6 . . ? N4 C11 C10 124.75(16) . . ? N4 C11 H11 116.1 . . ? C10 C11 H11 119.2 . . ? O2 C12 N5 125.29(14) . . ? O2 C12 C1 120.74(14) . . ? N5 C12 C1 113.95(14) . . ? N7 C13 N6 118.48(14) . . ? N7 C13 C14 122.66(15) . . ? N6 C13 C14 118.84(14) . . ? C15 C14 C13 118.62(15) . . ? C15 C14 H14 123.7 . . ? C13 C14 H14 117.7 . . ? C14 C15 C16 119.46(16) . . ? C14 C15 H15 120.5 . . ? C16 C15 H15 120.0 . . ? C17 C16 C15 118.10(16) . . ? C17 C16 H16 121.9 . . ? C15 C16 H16 119.9 . . ? N7 C17 C16 123.75(16) . . ? N7 C17 H17 115.4 . . ? C16 C17 H17 120.8 . . ? H3A O3 H3B 104.7 . . ? H3B O3A H3C 137.7 . . ? H3B O3A H3D 95.6 . . ? H3C O3A H3D 124.1 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2N O2 0.91 2.03 2.9277(17) 167.5 2_645 N3 H3N O3 0.92 1.99 2.8938(19) 170.1 . N3 H3N O3A 0.92 2.37 3.172(9) 145.7 . N5 H5N O2 0.89 2.04 2.8826(17) 158.8 2_645 N6 H6N N4 0.89 2.07 2.9537(18) 171.2 2_655 O3 H3A N7 0.78 2.01 2.7737(18) 166.1 3_776 O3A H3D N7 1.10 2.75 3.226(9) 105.6 3_776 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.10 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.318 _refine_diff_density_min -0.256 _refine_diff_density_rms 0.065 #===END OF ALL DATA